Toronto Maple Leafs: 5 Worst Free Agent Signings Of The Past Decade

TORONTO, CANADA - MARCH 29: Colby Armstrong #9 of the Toronto Maple Leafs skates with Wayne Simmonds #17 of the Philadelphia Flyers during NHL game action March 29, 2012 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images)
TORONTO, CANADA - MARCH 29: Colby Armstrong #9 of the Toronto Maple Leafs skates with Wayne Simmonds #17 of the Philadelphia Flyers during NHL game action March 29, 2012 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images) /
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The Toronto Maple Leafs have made some awful moves over the years. Let’s take a look at their five worst signings of the last decade.

The Toronto Maple Leafs have a long and storied history in the NHL. Bad roster management turned them into a laughing stock for the better half of a decade.

Teams are usually better off not opening their check book on July 1st. The Maple Leafs, as well the other 30 teams, seem to have ignored this. Building through the draft has, and always will be, the best course of action when running an NHL franchise. Drafting well keeps the window of contending open. In the salary cap era, mistakes in free agency can ruin a team for years to come.

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The key is to build a strong core that will be together for a long time and fill the rest of the roster out with young cheap options that can contribute. Once it’s time for the supplemental pieces on the team to get paid, trade them or let them walk, and find new cheap options to replace them. Teams that draft well can continue this cycle over and over again.

Free agency is truly a buyer’s beware. Unless an elite player hits the open market, which rarely happens, teams need to stay away. General managers can always find a way to convince themselves a player is worth it, but they won’t be.

With the signing of John Tavares, it is easy to forget the Leafs have made some awful free agent signings, resulting in a decade of awful teams. So have a lot of teams. But Toronto’s bad deals have cost them big time. Luckily, those days are over.

Let’s look back at the five worst deals the Leafs have signed in free agency over the last decade.